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Between oppressive temperatures and 100% humidity days, cities (New York, for one) can be downright cruel in the summer. Biking seems like a brilliant commuting alternative to a walk or the subway slog, but, then again…wind, exhaust, helmet head. Foiled. And even if the elements cooperate, how can you both functionally ride and look chic with all of the on-again, off-again moves required in a city?

We turned to Tokyobike North America owner Juliana Rudell di Simone to find out. She has a knack for looking effortlessly stylish when riding (all while on the coolest looking Tokyobike bike, of course).

You always look great when you ride. How do you approach dressing when you know you are biking?

I don’t think about the bike. I get dressed in the morning, and if I need to ride, I figure out a way that I can make any outfit work. My style is about comfort first (I don’t think I own a belt!). Anything too layered or too tight doesn’t work for me.


What pieces look chicest on a bike? 

Things that allow for movement. You’ll need it. Looking good on a bike is about prioritizing ease — nothing that will constrain your shoulders or inhibit you from reaching the handle bars.  That said, I don’t love cycling-specific clothing. I style my outfit to fit the bike ride as needed. Pants are always a good option—or jeans with room and stretch.

What are the best ways to style your look for biking?

I often wear a maxi dress and tie it up to become a short dress when I ride. I make sure to tie the hem up on the right-hand side, so that the fabric doesn’t get caught in the bike chain or spoke and wheel. If I’m wearing pants, I roll up the bottoms.

What is your favorite thing to ride in?

I like riding in flowy mini dresses—go figure—but they are comfortable, especially in the summer. Because they are loose, they hang and cover anything they need to cover. Sometimes I wear shorts underneath, too. I really like these tiny black cotton ones from Uniqlo ($29.90). They breathe nicely.

Product picks: the Ella Dress in Blue Flower by Rhode Resort ($365) or the Luis Dress by Weekend Max Mara (£250). 


How do you avoid looking sweaty post-ride? 

I embrace it—sweat becomes part of the glow I’m trying to achieve. And if I ride to a meeting, I carry tissues and space NK powder ($60) to put on my forehead. But it’s also a lot cooler on a bike than walking—you get the breeze!

What bag do you carry while biking?

In New York, I always carry too much. I sometimes turn the Mansur Gavriel tote ($585) and into a backpack, with one strap on each shoulder. It’s tall enough so nothing falls out. But a small crossbody is more ideal. I have a few I love that I’ve had forever—Alexander Wang, Chloe…

What shoes are best for riding?

Any flat shoes. I add a very thin layer of rubber on the bottom where the pedal hits to keep leather soles from slipping. Product picks: the Pinnacle Nike Air Max ($150) or Golden Goose sneaker from Ssense ($480).

Do you add anything to your bike to make riding easier (and chicer)?

I keep my bike super simple—I love the salmon red color on its own. But a lock and a light are important. Product picks: the Classic Sport Tokyobike ($825), Tokyobike Magnetic Lights ($40), and the Tokyobike Universal Bell ($20). How would you describe your personal style for biking?  Comfort is it. That’s all!


This story is part of our special 100 Days of Summer series. You can find more tips and fun ideas here.

Related reading:

The Domino Bike by Pure City The Only Workouts You Should do at Night How a Fitness Guru Balances Life with a New Baby 

Second and third image via @tokyobike_nyc on Instagram.